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Derivatives of Norbornanes Having Hydrocarbon Side Chains, Processes for Preparing the Same and Perfume Compositions Containing the Same

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Derivatives of Norbornanes Having Hydrocarbon Side Chains, Processes for Preparing the Same and Perfume Compositions Containing the Same Europaisches Patentamt European Patent Office © Publication number: 0 059 457 Office europeen des brevets A1 © EUROPEAN PATENT APPLICATION © Application number: 82101503.9 ©mtci.3: C 07 C 47/347 C 07 C 47/45, C 07 C 31/137 @ Date of filing: 26.02.82 C 07 C 33/16, A 61 K 7/46 C 07 C 29/38, C 07 C 45/41 C 07 C 45/50, C 07 C 45/58 C 07 C 45/62 © Priority: 28.02.81 JP 29188/81 © Applicant: Nippon Petrochemicals Co., Ltd. 28.02.81 JP 29189/81 Saiwai Building, 1-3-1 Uchisaiwai-cho Chiyoda-ku 22.08.81 JP 131743/81 Tokyo(JP) 22.08.81 JP 131744/81 © Inventor: Inoue, Yoshiharu 16-24, Imaichi 2-chome Asahi-ku © Date of publication of application: Osaka-shi Osaka-fu(JP) 08.09.82 Bulletin 82736 © Inventor: Tanimoto, Fumio 471, Muromachi Nishiiru © Designated Contracting States: Santeicho CH DE FR GB LI NL Nakadachiuri-dori Kamigyo-ku Kyoto-shi Kyoto-fu(JP) © Inventor: Kitano, Hisao 1-6-205, Harimacho 3-chome Abeno-ku Osaka-shi Osaka-f u(JP) © Representative: Schubel-Hopf, Ursula, Dr. et al, K.L. Schiff Dr. A. v. Funer Dipl.-lng. P. Strehl Dr. U. Schubel-Hopf Dipl.-lng. D. Ebbinghaus Dr.lng. D .Finck Patentanwalte Mariahilf platz 2 & 3 D-8000 Munchen 90(DE) © Derivatives of norbornanes having hydrocarbon side chains, processes for preparing the same and perfume compositions containing the same. ©Norbornane Norbornane derivatives having hydrocarbon side chains, the processes for preparing the same and perfume compositions containing the same. The norbornanenorbomane deriva-(I)� tives are represented by the following general formula (I) (11) 3 wherein R4 is a methyl group, an ethyl group,group,gn a n-propyl a (1), 1 » group or an isopropyl group, and X is a carboncarl atom of the norbornanenorbomane ring. The above norbornane derivativesde give a wide variety of woody fragrances and are uiuseful as compo- nents for various perfume products. in 1 wherein C2 is an ethyl group, an ethylidene group or a vinyl group each connected to 5 or 6 position of the norbornane 0) ring, each of R, and R2 is a hydrogen atom or a methyl group, and R3 is a formyl group or a group represented by the o following general formula (II) Q. LU Croydon Printing Company Ltd. BACKGROUND OF THE INVENTION 1. Field of the Invention . This invention relates to derivatives of norbornanes, processes for preparing the same and perfume compositions containing the.same. More particularly, the invention relates to novel derivatives of norbornanes having hydrocarbon side chains, especially, saturated or unsaturated hydrocarbons containing two carbon atoms, processes for preparing the same and perfume compositions containing the same. 2. Description of the Prior Art A variety of synthetic perfume components have been prepared in order to make up for or to use in place of expensive natural perfume components. For example, compounds having norbornane bicyclo-(2,2,1)-heptane ring are proposed in several references. U.S. Patent No. 3,673,261 and No. 3,673,263 disclose 2-methyl-3-(5'-hydroxyalkenyl)-norbornanes. U.S. Patent No. 3,748,344 discloses a process for preparing cyclic acetals of norbornane carboxyaldehydes. U.S. Patent No. 3,860,635 discloses a process for preparing.vinyl norbornanone. Further, disclosed in U.S. Patent No. 4,076,853 are various kinds of alpha-allyl or methallyl-3,3-dimethyl- 2-norbornyl methanols. However, in connection with the specific norbornane derivatives having hydrocarbon side chains containing two carbon atoms of the present invention, no disclosure is found. BRIEF SUMMARY OF THE INVENTION The present invention is based upon the fact that the inventors found novel norbornane derivatives, processes for preparing the same and perfume compositions containing the same, as described below. The object of the present invention is, therefore, to provide such a new finding. The present invention relates to derivatives of norbornanes having hydrocarbon side chains, processes for preparing the same and perfume compositions containing the same. The norbornane derivatives of the invention are represented by the following general formula (I) wherein C2 is an ethyl group, an ethylidene group or a vinyl group each connected to 5 or 6 position of the norbornane ring, the dashed line connected to C2 is a single bond when C2 is an ethyl group or a vinyl group and a double bond when C2 is an ethylidene group, each of R1 and R2 is a hydrogen atom or a methyl group, and R3 is a formyl group or a group represented by the following general formula (II) wherein R4 is a methyl group, an ethyl group, a n-propyl group or an isopropyl group, the combination of a solid line with a dotted line indicates a single bond or a double bond, and X is a carbon atom of the norbornane ring. According to the present invention, the norbornane derivatives represented by the foregoing general formula (I) can be prepared by hydrolyzing and decarboxylating glycidic esters represented by the following general formula (III) at temperatures in the range of 0 to 250°C wherein C2, dashed line, R1and R2 are respectively the same as those in the foregoing general formula (I) and R5 is a hydrocarbon group having 1 to 6 carbon atoms. Through this process, a norbornane derivative of formula (I) having a formyl group as R3 can be prepared. The inventors have found another method to prepare the norbornane derivative of formula (I) having a formyl group as R3 by reacting 2-norbornene represented by the following general formula (IV) with carbon monoxide and hydrogen gas in the presence of a catalyst at temperatures in the range of 30 to 300°C wherein C2, dashed line and R1 are respectively the same as those in the formula (I). The reaction product.in this process has a hydrogen atom as R2 and'a formyl group as R3 in the foregoing general formula (I). Further, when R3 is not a formyl group but a group represented by the foregoing general formula (II), the product obtained from any one of the above processes, that is, a norbornyl aldehyde, is reacted with ethyl alkyl ketone in the presence of an aldol condensation catalyst at temperatures in the range of 0 to 200oC and thereafter the reaction product is subjected to dehydration and reduction, thereby obtaining the norbornane derivative of formula (I) having a group of formula (II) as R3. Also included in the present invention is perfume compositions containing the norbornane derivatives representec by the above-defined formula (I). DETAILED DESCRIPTION OF THE INVENTION The present invention will now be described in more detail. As described above, the norbornane derivatives of the present invention are represented by the following general formula (I) wherein C2 is an ethyl group, an ethylidene group or a vinyl group each connected to 5 or 6 position of the norbornane ring, the dashed line connected to C2 is a single bond when C2 is an ethyl group or a vinyl group and a double bond when C2 is an ethylidene group, each of R1 and R2 is a hydrogen atom or a methyl group, and R3 is a formyl group or a group represented by the following general formula (II) wherein R4 is a methyl group, an ethyl group, a n-propyl group or an isopropyl group, the combination of a solid line with a dotted line indicates a single bond or a double bond, and X is a carbon atom of the norbornane ring. The compounds included in the above norbornane derivatives represented by the general formula (I) are: 5- or 6-ethylnorbornyl-2-aldehyde, 5- or 6-ethylidenenorbornyl-2-aldehyde, 5- or 6-vinylnorbornyl-2-aldehyde, their 3-methyl derivatives and 3,3-dimethyl derivatives, and 4-(5'- or 6'-ethylnorbornan-2'-yl)-3-methylbutan-2-ol, 4-(5'- or 6'-ethylidenenorbornan-2'-yl)-3-methylbutan-2-ol, 4-(5'- or 6'-vinylnorbornan-2'-yl)-3-methylbutan-2-ol, 4-(5'- or 6'-ethylnorbornan-2'-yl)-3-methyl-3-buten-2-ol, 4-(5'- or 6'-ethylidenenorbornan-2'-yl)-3-methyl-3-buten-2-ol, 4-(5'- or 6'-vinylnorbornan-2'-yl)-3-methyl-3-buten-2-ol, 1-(5'- or 6'-ethylnorbornan-2'-yl)-2-methylpentan-3-ol, 1-(5'- or 6'-ethylidenenorbornan-2'-yl)-2-methylpentan-3-ol, 1-(5'- or 6'-vinylnorbornan-2'-yl)-2-methylpentan-3-ol, 1-(5'- or 6'-ethylnorbornan-2'-yl)-2-methyl-1-penten-3-ol, 1-(5'- or 6'-ethylidenenorbornan-2'-yl)-2-methyl-1-penten-3-ol, 1-(5'- or 6'-vinylnorbornan-2'-yl)-2-methyl-l-penten-3-ol, 1-(5'- or 6'-ethylnorbornan-2'-yl)-2,4-dimethylpentan-3-ol, 1-(5'- or 6'-ethylidenenorbornan-2'-yl)-2,4-dimethyl- pentan-3-ol, 1-(5'- or 6'-vinyInorbornan-2'-yl)-2,4-dimethylpentan-3-ol, 1-(5'- or 6'-ethylnorbornan-2'-yl)-2,4-dimethyl-1-penten-3-ol, 1-(5'- or 6'-ethylidenenorbornan-2'-yl)-2,4-dimethyl-1- penten-3-ol, 1-(5'- or 6'-vinylnorbornan-2'-yl)-2,4-dimethyl-1-penten-3-ol, 1-(5'- or 6'-ethylnorbornan-2'-yl)-2-methylhexan-3-ol, 1-(5'- or 6'-ethylidenenorbornan-2'-yl)-2-methylhexan-3-ol, 1-(5'- or 6'-vinylnorbornan-2'-yl)-2-methylhexan-3-ol, 1-(5'- or 6'-ethylnorbornan-2'-yl)-2-methyl-l-hexen-3-ol, 1-(5'- or 6'-ethylidenenorbornan-2'-yl)-2-methyl-l-hexen-3-ol, 1-(5'- or 6'-vinylnorbornan-2'-yl)-2-methyl-1-hexen-3-ol, their 3'-methyl derivatives and 3',3'-dimethyl derivatives.
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